L-Lysine

L-Lysine Basic information
Product Name:L-Lysine
Synonyms:L-Lysine crystallized, >=98.0% (NT);L-Lysine Vetec(TM) reagent grade, >=98%;NEODIMIUM STAND;(S)-2,6-DIAMINOCAPROIC ACID;(S)-(+)-LYSINE;L-Lysine≥ 99% (Titration);LYSINE, L-(+)-;L-(+)-LYSINE
CAS:56-87-1
MF:C6H14N2O2
MW:146.19
EINECS:200-294-2
Product Categories:Nutritional Supplements;Amino Acids;alpha-Amino Acids;Biochemistry;Amino Acid Derivatives;Lysine [Lys, K];Amino Acids;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Thiazines ,Halogenated Heterocycles ,Thiazoles;Food additives;56-87-1
Mol File:56-87-1.mol
L-Lysine Structure
L-Lysine Chemical Properties
Melting point 215 °C (dec.)(lit.)
alpha D20 +14.6° (c = 6.5); D23 +25.9° (c = 2 in 6.0N HCl)
Boiling point 265.81°C (rough estimate)
density 1.1360 (rough estimate)
refractive index 26 ° (C=2, 5mol/L HCl)
FEMA 3847 | L-LYSINE
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility H2O: 0.1 g/mL, clear, colorless
pka2.16(at 25℃)
form Powder or Crystals
color White to light yellow
Odorodorless
optical activity[α]20/D +26.0±1.0°, c = 2% in 6 M HCl
Water Solubility Soluble in water. Insoluble in ethanol, ethyl ether, acetone, benzene and common neutral solvent.
JECFA Number1439
Merck 14,5636
BRN 1722531
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyKDXKERNSBIXSRK-YFKPBYRVSA-N
LogP-3.05
CAS DataBase Reference56-87-1(CAS DataBase Reference)
NIST Chemistry ReferenceLysine(56-87-1)
EPA Substance Registry SystemLysine (56-87-1)
Safety Information
Hazard Codes Xi
Safety Statements 24/25
WGK Germany 3
RTECS OL5540000
TSCA Yes
HS Code 29224110
Hazardous Substances Data56-87-1(Hazardous Substances Data)
MSDS Information
ProviderLanguage
L-Lysine English
SigmaAldrich English
L-Lysine Usage And Synthesis
DescriptionSee ι-LYSINE MONOCHLORIDE.
Chemical PropertiesL-Lysine is an essential amino acid (a protein building block) that cannot be produced by the body from other nutri ents. It helps ensure adequate absorption of calcium and the formation of collagen for bone, cartilage and connective tissue. This compound is odorless.
Chemical PropertiesWhite to pale yellow crystalline powder
OccurrenceSome natural food sources for l-lysine include lima beans, kidney beans, potatoes, corn, red meat, fish and milk.
UsesEssential amino acid for human development. Lysine residues are useful in many cellular processes, due to their ability to accept a wide variety of post-translational modifications.
UsesA moderate serotonin antagonist and essential amino acid.
Useslysine is a skin-conditioning amino acid.
UsesL-Lysine is an essential amino acid used in human nutrition. It plays a vital role in calcium absorption, building muscle protein and recovering from surgery or sports injuries. It is used for the treatment of herpes infections and cold sores. Its derivatives lysine acetylsalicylate is utilized to treat pain as well as to detoxify the body after heroin use. It is an important additive to animal feed. Further, it is used in many foods, especially red meats, fish and dairy products.
PreparationProduced by fermentation. Also produced by use of continuous ion exchange technology.
DefinitionChEBI: An L-alpha-amino acid; the L-isomer of lysine.
Biotechnological ProductionC. glutamicum and, to a lesser extent, E. coli are the main organisms used today for industrial L-lysine production. The first L-producing strains based on C. glutamicum were reported in 1961, and those based on E. coli in 1995. The advantages of using E. coli versus C. glutamicum include the achievement of higher growth rates at higher fermentation temperatures. The formation of lysine is highly influenced by two enzymes, aspartate kinase (AK) and homoserine dehydrogenase (HDH). AK converts aspartate into aspartate semialdehyde, and is highly feedback-inhibited by lysine and threonine. HDH converts aspartate semialdehyde into homoserine, which is an intermediate for the biosynthesis of threonine, methionine, and isoleucine. L-Lysine–producing strains therefore often contain a deregulated AK and/or a reduced activity HDH. Despite the improvement of the flux from aspartate towards lysine, the availability of key metabolites from the central metabolic pathways is also essential. Here the formation of oxaloacetate directly from phosphoenol pyruvate or via pyruvate is essential for the carbon yield as some unnecessary cycles are included. For example, inactivation of the enzyme phosphoenol pyruvate carboxykinase, which catalyzes the reverse reaction from oxaloacetate to phosphoenol pyruvate gave an improvement in lysine formation. By overexpression of pyruvate carboxylase, the conversion yield of glucose to lysine could be increased by 50 %. With a synthetic lysine hyperproducing strain, containing 12 defined modifications from the wild type, a carbon yield of 0.55 g/g and a product titer of 120 g/L over 30 h fermentation could be obtained.
Today, however, the main commercial process for L-lysine remains the fermentation of C. glutamicum. This is performed in fed-batch mode in large-scale fermenters of up to 500 m3 volume, with production capacities in excess of 100,000 tonnes. The commercial manufacturing process has been comprehensively described by Pfefferle.
Aroma threshold valuesDetection: 500 ppm
Synthesis Reference(s)Journal of the American Chemical Society, 71, p. 3161, 1949 DOI: 10.1021/ja01177a063
General DescriptionL-Lysine is a basic amino acid.
Safety ProfileAn experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Veterinary Drugs and TreatmentsLysine may be effective in suppressing FHV-1 infections in cats.
Purification MethodsCrystallise L-lysine from aqueous EtOH. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2097-2122 1961, Kearley & Ingersoll J Am Chem Soc 73 5783 1951, Beilstein 4 IV 2717.]
BOC-N-EPSILON-NICOTINOYL-D-LYSINE,BOC-N-EPSILON-NICOTINOYL-D-LYSINE BOC-N-EPSILON-ALLYLOXYCARBONYL-L-LYSINE DICYCLOHEXYL AMMONIUM SALT,BOC-N-EPSILON-ALLYLOXYCARBONYL-L-LYSINE DICYCLOHEXYL AMMONIUM SALT BOC-N-EPSILON-(2-CHLORO-Z)-L-LYSINE,BOC-N-EPSILON-(2-CHLORO-Z)-L-LYSINE BOC-N-EPSILON-CARBAMOYL-D-LYSINE,BOC-N-EPSILON-CARBAMOYL-D-LYSINE BOC-N-EPSILON-FORMYL-L-LYSINE,BOC-N-EPSILON-FORMYL-L-LYSINE Fmoc-N'-methyltrityl-L-lysine BOC-N-EPSILON-ISOPROPYL-N-EPSILON-Z-L-LYSINE,BOC-N-EPSILON-ISOPROPYL-N-EPSILON-Z-L-LYSINE BOC-N-EPSILON-CARBAMOYL-L-LYSINE,BOC-N-EPSILON-CARBAMOYL-L-LYSINE BOC-N-EPSILON-Z-D-LYSINE,BOC-N-EPSILON-Z-D-LYSINE BOC-N-EPSILON-ISOPROPYL-L-LYSINE,BOC-N-EPSILON-ISOPROPYL-L-LYSINE BOC-N-EPSILON-(2-CHLORO-Z)-D-LYSINE,BOC-N-EPSILON-(2-CHLORO-Z)-D-LYSINE BOC-N-ALPHA-METHYL-N-EPSILON-Z-L-LYSINE,BOC-N-ALPHA-METHYL-N-EPSILON-Z-L-LYSINE BOC-N-EPSILON-FORMYL-L-LYSINE,BOC-N-EPSILON-FORMYL-L-LYSINE BOC-N-EPSILON-DIMETHYL-L-LYSINE,BOC-N-EPSILON-DIMETHYL-L-LYSINE Theophylline lysine BOC-N-EPSILON-NICOTINOYL-L-LYSINE,BOC-N-EPSILON-NICOTINOYL-L-LYSINE BOC-N-EPSILON-2-BROMO-Z-L-LYSINE,BOC-N-EPSILON-2-BROMO-Z-L-LYSINE BOC-N-EPSILON-2-CHLORO-Z-L-LYSINE T-BUTYLAMINE,BOC-N-EPSILON-2-CHLORO-Z-L-LYSINE T-BUTYLAMINE

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